HCID 10926284, compound → HCID 14947808, compound

HRID 2259409Notes

Reaction equation

HRID 2259409 reaction equation
[C:1]([O:9][CH2:10][C@@H:11]1[C@@H:15]([CH2:16][O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:14][CH:13]([OH:26])[CH2:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO>[C:18]([O:17][CH2:16][C@@H:15]1[C@@H:11]([CH2:10][O:9][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:12][C:13](=[O:26])[CH2:14]1)(=[O:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

3

Reactant 1

HCID 10926284HCID 10926284, compound2×

Product 1

HCID 14947808HCID 14947808, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(3S,4S)-3,4-di(benzoyloxymethyl)cyclopentanol (compound 9, Scheme 2). To the compound 8 obtained under a) (193 mg, 0,55 mmol) in methanol (10 ml) was added sodium borohydride (41 mg, 1,10 mmol) in successive portions. The mixture was stirred at room temperature for 30 min, and then diluted with water and diethyl ether. The organic layer was washed with saturated aqueous sodium chloride, dried (MgSO4) and concentrated to a syrup which was purified by column chromatography on silica gel (toluen/EtOAc, 1:1) to yield title compound (189 mg, 97%; [α]D -16.4° (c 1.09, chloroform); 1H NMR (100 MHz, CDCl3) δ1.6-2.7 (m, 7H, 2 CH, 2 CH2, OH), 4.41 (t, 4H, 2 CH2 -OBz), 7.34-7.56 and 7.97-8.09 (m, 10H, aromatic H); 13C NMR (25.05 MHz, CDCl3) δ38.3, 39.3, 39.8, 40.0 (2 CH2 2 CH), 67.4, 68.2 (2 CH2 -OBz), 72.5 (CHOH), 128.1, 129.3, 129.8, 132.8 (aromatic C), 166.3 (C=O). Anal. Calcd for C21H22O5 (354.4): C, 71.17; H, 6.26. Found: C, 71.05; H, 6.18.

Sources & evidence

ORD record
ord-852af8d8bb18438db1e0a34b348233e9
Source dataset
uspto-grants-1995_12
Patent number
US05473063

Reaction notes

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