Hydrochloric Acid → 3alpha-Hydroxy-17beta-isopropoxycarbonyl-5alpha-androstan-11-one

HRID 267611Notes

Reaction equation

[OH:1][C@@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[C:15](=[O:21])[CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:22]([OH:24])=[O:23])[CH2:3]1.Cl.[CH:26](O)([CH3:28])[CH3:27]>>[OH:1][C@@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[C:15](=[O:21])[CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:22]([O:24][CH:26]([CH3:28])[CH3:27])=[O:23])[CH2:3]1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 3776Isopropanol

HCID 227882653alpha-Hydroxy-5alpha-androstan-11-one 17beta-carboxylic acid

Product 1

HCID 867331283alpha-Hydroxy-17beta-isopropoxycarbonyl-5alpha-androstan-11-one

Procedure

A solution of 3α-hydroxy-11-oxo-5α-androstane-17β-carboxylic acid (550 mg.) in dry isopropanol containing 3.7%, by weight, of hydrogen chloride (100 ml.) was refluxed for 61/2 hours.

Sources & evidence

ORD record: ord-661d0e7f4f594f91adf66380dd82cb6b
Source dataset: uspto-grants-1976_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03943124

Reaction notes

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