HCID 10926284, compound → HCID 14947808, compound

HRID 618440Notes

Reaction equation

HRID 618440 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) δ 1.6-2.7 (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) δ 38.3, 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 (3 54.4): C, 71.17; H, 6.26. Found: C, 71.05; H, 6.18.

Sources & evidence

ORD record
ord-dbd228df96c24724afd535d3b17f9a7a
Source dataset
uspto-grants-1999_09
Patent number
US05952500

Reaction notes

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