Methanol → HCID 58002951, compound

HRID 1516737Notes

Reaction equation

HRID 1516737 reaction equation
N[C@@H]1C2C(=CC=CC=2)C[C@@H]1O.[CH:12]([C:15]1[CH:24]=[C:23]2[C:18]([C:19](=[O:27])[CH2:20][C:21]([CH3:26])([CH3:25])[O:22]2)=[C:17]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:16]=1[C:34](=[O:46])[C:35]1[CH:40]=[CH:39][C:38]([O:41][C:42]([F:45])([F:44])[F:43])=[CH:37][CH:36]=1)([CH3:14])[CH3:13].CO>O1CCCC1>[OH:27][C@@H:19]1[C:18]2[C:23](=[CH:24][C:15]([CH:12]([CH3:13])[CH3:14])=[C:16]([C:34]([C:35]3[CH:40]=[CH:39][C:38]([O:41][C:42]([F:45])([F:43])[F:44])=[CH:37][CH:36]=3)=[O:46])[C:17]=2[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[O:22][C:21]([CH3:25])([CH3:26])[CH2:20]1

Participants

5

Reactant 3

HCID 887MethanolHCID 2725045(1R,2S)-(+)-cis-1-Amino-2-indanolHCID 58002955HCID 58002955, compound

Product 1

HCID 58002951HCID 58002951, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

72 μl (410 μmol) of borane/N,N-diethylaniline complex are added slowly to a solution of 2.3 mg (20 μmol) of (1R,2S)-1-aminoindan-2-ol in 1.5 ml of tetrahydrofuran, and the mixture is stirred for 30 min. The mixture is then cooled to 0° C., and a solution of 49 mg (100 μmol) of 7-isopropyl-2,2-dimethyl-5-phenyl-6-[4-(trifluoromethoxy)benzoyl]-2,3-dihydro-4H-chromen-4-one (Example 32A) in 3.5 ml of tetrahydrofuran is slowly added dropwise. The mixture is allowed to thaw slowly and stirred at room temperature overnight. Methanol is then added, and the solvent is removed under reduced pressure. The residue is taken up in ethyl acetate and washed in each case twice with 1 M hydrochloric acid and saturated sodium bicarbonate solution and once with saturated sodium chloride solution. The organic phase is dried over sodium sulfate and then concentrated under reduced pressure. Purification of the residue by preparative HPLC (method 1) gives the target product.

Workup

  1. stirringstirred at room temperature overnight
  2. customthe solvent is removed under reduced pressure
  3. washwashed in each case twice with 1 M hydrochloric acid and saturated sodium bicarbonate solution and once with saturated sodium chloride solution
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customPurification of the residue by preparative HPLC (method 1)
  7. customgives the target product

Sources & evidence

ORD record
ord-e8514862306849f59f1ac95e05116318
Source dataset
uspto-grants-2012_07
Patent number
US08227511B2

Reaction notes

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