Acetic Acid → HCID 86584402, compound

HRID 2227240Notes

Reaction equation

[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C:14]([CH2:15][C:16](=[O:24])[CH2:17][CH2:18]1)=[CH:13][C@H:12]3[CH3:25])(=[O:3])[CH3:2].[BH4-].[Na+].C(O)(=O)C>O1CCCC1.C(O)C>[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C:14]([CH2:15][C@@H:16]([OH:24])[CH2:17][CH2:18]1)=[CH:13][C@H:12]3[CH3:25])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: -3 °C

Procedure

Add slowly a solution of 7α-methylandrost-5-en-3-on-17β-ol 17 acetate (L74a, 6.3 g, 18.9 mmol) in tetrahydrofuran (50 mL) to a solution of sodium borohydride (0.72 g, 18.9 mmol) in 95% ethanol (200 mL) cooled to −3° C. in a salt/ice bath with stirring. Stir at this temperature for 3 hours and decompose the excess reagent by cautious addition of acetic acid (10 mL). Remove the solvents and purify the resulting crude product by flash chromatography to give 7α-methylandrost-5-ene-3β,17β-diol 17 acetate (L75a) as a white solid. Similarly prepare the following analogs:

Workup

stirringStir at this temperature for 3 hours
customRemove the solvents
custompurify the resulting crude product by flash chromatography

Sources & evidence

ORD record: ord-42566252ef144f76a91e531e4f28687e
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06413951B2

Reaction notes

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