HCID 10926284, compound → HCID 14947808, compound

HRID 1954440Notes

Reaction equation

HRID 1954440 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 (354.4): C, 71.17; H, 6.26. Found: C, 71.05; H, 6.18.

Sources & evidence

ORD record
ord-a22ad1df85f3480d90bedaac6d11475d
Source dataset
uspto-grants-2000_09
Patent number
US06121431

Reaction notes

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