Potassium borohydride → HCID 11738397, compound

HRID 1660698Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:5](=[O:21])[C@H:6]([NH:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[CH:7]([CH3:9])[CH3:8].[BH4-].[K+]>CO>[CH3:1][O:2][C:3](=[O:22])[CH2:4][C@H:5]([OH:21])[C@H:6]([NH:10][C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12])[CH:7]([CH3:9])[CH3:8]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of methyl ester 11 (2.8 g, 9.15 mmol) in HPLC MeOH (30 mL), cooled to −78° C., potassium borohydride (1.72 g, 32 mmol) was added in portions. The reaction mixture was stirred at −78° C. for 10 min, warmed to −20° C. for 30 min and then to 0° C. for 10 min. The reaction was quenched with acetic acid to pH 7 and extracted with CH2Cl2 (3×50 mL). The organic layer was washed with NaHCO3 (50 mL, sat), NaCl (50 mL, sat), dried (Na2SO4), filtered and evaporated. The alcohol 12 was obtained as a colorless oil (2.7 g, 98%) and used directly in the next step. 1H-NMR (500 MHz, CDCl3): 0.87 (d, J=6.7 Hz, 3H), 0.94 (d, J=6.7 Hz, 3H), 2.10-2.19 (m, 1H), 2.47 (dd, J=16.7 and 9.1 Hz), 2.58 (dd, J=16.7 and 2.9 Hz, 1H), 3.11-3.20 (m, 1H), 3.56-3.63 (m, 1H), 3.68 (s, 3H), 3.90-3.98 (m, 1H), 4.64 (d, J=7.9 Hz, 1H), 5.09 (s, 2H), 7.30-7.39 (m, 5H).

Workup

temperaturewarmed to −20° C. for 30 min
waitto 0° C. for 10 min
customThe reaction was quenched with acetic acid to pH 7
extractionextracted with CH2Cl2 (3×50 mL)
washThe organic layer was washed with NaHCO3 (50 mL, sat), NaCl (50 mL, sat)
dry with materialdried (Na2SO4)
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-ffb8b69a5fca40b59e5a2be71ff0c4a6
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030279B2

Reaction notes

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