Acetic Anhydride → HCID 131722680, compound

HRID 2301166Notes

Reaction equation

HRID 2301166 reaction equation
[CH:1]1([CH2:6][C@@H:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[OH:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:15](OC(=O)C)(=[O:17])[CH3:16]>N1C=CC=CC=1>[C:15]([O:8][C@H:7]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH2:6][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)(=[O:17])[CH3:16]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 54202943HCID 54202943, compound

Product 1

HCID 131722680HCID 131722680, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 406 mg (2.13 mmol) of (S)-2-cyclopentyl-1-phenylethanol (from Step C) in 9 mL of pyridine was treated with 1 mL of acetic anhydride. After stirring for 6 h, the reaction was concentrated. Flash chromatography on silica gel using 93:7 v/v hexanes/EtOAc afforded 495 mg (100%) of the title compound: RF: 0.75 (4:1 v/v hexanes/EtOAc); 1H NMR (300 MHz): δ 1.10-1.21 (m, 2H), 1.44-2.04 (m, 9H), 2.05 (s, 3H), 5.75 (dd, J=8.0, 6.1, 1H), 7.25-7.34 (m, 5H).

Workup

  1. concentrationthe reaction was concentrated

Sources & evidence

ORD record
ord-dd3212e49f304582883a102886ebf700
Source dataset
uspto-grants-2002_12
Patent number
US06498161B1

Reaction notes

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