HCID 10926284, compound → HCID 14947808, compound

HRID 1288797Notes

Reaction equation

HRID 1288797 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-31db9d9c7b88409e863f27790b855e85
Source dataset
uspto-grants-1998_05
Patent number
US05747473

Reaction notes

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