Acetic Anhydride → HCID 66761416, compound

HRID 573773Notes

Reaction equation

HRID 573773 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15]2[N+:14]([O-])=[C:13]([CH:22]([CH3:24])[CH3:23])[C:12]3[C@@H:25]([C:32]4[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=4)[O:26][C:27]4([CH2:31][CH2:30][CH2:29][CH2:28]4)[C:11]=3[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:42]([O:45]C(=O)C)(=[O:44])[CH3:43]>>[C:42]([O:45][C@@H:16]1[C:15]2[N:14]=[C:13]([CH:22]([CH3:24])[CH3:23])[C:12]3[C@@H:25]([C:32]4[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=4)[O:26][C:27]4([CH2:31][CH2:30][CH2:29][CH2:28]4)[C:11]=3[C:10]=2[C@@H:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:18][C:17]1([CH3:20])[CH3:19])(=[O:44])[CH3:43]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 66763382HCID 66763382, compound

Product 1

HCID 66761416HCID 66761416, compound

Conditions

Temperature
130 °C

Procedure

250 mg (3′R,9′S)-9′-(tert-butyldimethylsilyloxy)-4′-isopropyl-7′,7′-dimethyl-3′-(4-(trifluoromethyl)phenyl)-6′,7′,8′,9′-tetrahydro-3′H-spiro[cyclopentane-1,1′-furo[3,4-c]quinoline]5′-oxide and 3 ml acetic acid anhydride are mixed and heated for 2 hours at 130° C. Excess acetic acid anhydride is removed in vacuo and the residue is diluted with diethylether. After washing with saturated aqueous sodium bicarbonate the organic phase is dried with sodium sulphate. The solvent is evaporated in vacuo and the residue is chromatographed on silica gel (hexane/ethylacetate 95:5).

Workup

  1. customExcess acetic acid anhydride is removed in vacuo
  2. additionthe residue is diluted with diethylether
  3. washAfter washing with saturated aqueous sodium bicarbonate the organic phase
  4. dry with materialis dried with sodium sulphate
  5. customThe solvent is evaporated in vacuo
  6. customthe residue is chromatographed on silica gel (hexane/ethylacetate 95:5)

Sources & evidence

ORD record
ord-715c50a35e6f489f8ec92fa816e6a2dc
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

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