(2S)-2-((8S,9S,10R,13S,14S,17R)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta(a)phenanthren-17-yl)propanal → HCID 11142115, compound

HRID 566883Notes

Reaction equation

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

Participants

Conditions

Temperature: -10 °C

Procedure

i)—A solution of (20S)-3-oxopregn-4-ene-20-carboxaldehyde (2) (125 g) in dry ethanol (1250 ml) was cooled to −10° C., whereupon a solution of sodium borohydride (4.4 g) in dry ethanol (80 ml) was added in 30 min. After stirring the mixture for 2 h at −10° C., the reaction was quenched by adding a 50% aqueous solution of acetic acid. The reaction mixture was concentrated under reduced pressure to 25% of its original volume and then poured into ice-water (5 l). The resulting suspension was stirred overnight and filtered. The residue was washed with water and dried to give (20S)-21-hydroxy-20-methylpregn-4-en-3-one (3) (124 g) which was used in the following step without further purification.

Workup

additionwas added in 30 min
customthe reaction was quenched
additionby adding a 50% aqueous solution of acetic acid
concentrationThe reaction mixture was concentrated under reduced pressure to 25% of its original volume
additionpoured into ice-water (5 l)
stirringThe resulting suspension was stirred overnight
filtrationfiltered
washThe residue was washed with water
customdried

Sources & evidence

ORD record: ord-a90f26aa768f466a8dd381ddbebac47d
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06177420B1

Reaction notes

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