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Methanol → (S)-4-Isopropyl-9-hydroxy-7,7-dimethyl-2',3',5',6,6',7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4'-pyran]-3-one

HRID 573800
Notes
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Reaction equation

HRID 573800 reaction equation
C1C2C(=CC=CC=2)[C@@H](N)[C@H]1O.B.CCN(C1C=CC=CC=1)CC.[CH:24]([C:27]1[C:36]2[C:37](=[O:45])[O:38][C:39]3([CH2:44][CH2:43][O:42][CH2:41][CH2:40]3)[C:35]=2[C:34]2[C:33](=[O:46])[CH2:32][C:31]([CH3:48])([CH3:47])[CH2:30][C:29]=2[N:28]=1)([CH3:26])[CH3:25].CO>O1CCCC1>[OH:46][C@H:33]1[CH2:32][C:31]([CH3:48])([CH3:47])[CH2:30][C:29]2[N:28]=[C:27]([CH:24]([CH3:26])[CH3:25])[C:36]3[C:37](=[O:45])[O:38][C:39]4([CH2:40][CH2:41][O:42][CH2:43][CH2:44]4)[C:35]=3[C:34]1=2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 83312Diethylaniline-boraneHCID 2725045(1R,2S)-(+)-cis-1-Amino-2-indanolHCID 667623744-Isopropyl-7,7-dimethyl-2',3',5',6',7,8-hexahydro-3H-spiro[furo[3,4-c]quinoline-1,4'-pyran]-3,9(6H)-dione

Product 1

HCID 66761429(S)-4-Isopropyl-9-hydroxy-7,7-dimethyl-2',3',5',6,6',7,8,9-octahydro-3H-spiro[furo[3,4-c]quinoline-1,4'-pyran]-3-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

0.700 g (1R,2S)-(+)-cis-1-Amino-2-indanol are dissolved in 150 ml tetrahydrofurane and to this solution are dropwise added 6.12 ml of a borane-diethylaniline-complex. After completion of gas evolution the solution is cooled to 0° C. and 5.54 g 4-Isopropyl-7,7-dimethyl-2′,3′,5′,6′,7,8-hexahydro-3H-spiro[furo[3,4-c]quinoline-1,4′-pyran]-3,9(6H)-dione in 150 ml tetrahydrofurane are added dropwise. The temperature is raised during 2 hours to room temperature and the mixture is stirred for 24 hours. 10 ml Methanol are added dropwise and the solvents are evaporated in vacuo. The residue was dissolved in dichloromethane and is washed with 0.1 M hydrochloric acid and saturated aqueous sodium bicarbonate solution consecutively. The combined organic phases are dried with sodium sulphate and the solvents are evaporated in vacuo. The residue is chromatographed on silica gel (petrole ether/ethylacetate 100:0 to 3:2).

Workup

  1. temperatureThe temperature is raised during 2 hours to room temperature
  2. customthe solvents are evaporated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washis washed with 0.1 M hydrochloric acid and saturated aqueous sodium bicarbonate solution consecutively
  5. dry with materialThe combined organic phases are dried with sodium sulphate
  6. customthe solvents are evaporated in vacuo
  7. customThe residue is chromatographed on silica gel (petrole ether/ethylacetate 100:0 to 3:2)

Sources & evidence

ORD record
ord-50ad07f2a7654d92bb22574c2b769251
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09029544B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes