HCID 86734295, compound → 21-Formyl-3alpha-hydroxy-5alpha-pregnane-11,20-dione

HRID 1973726Notes

Reaction equation

HRID 1973726 reaction equation
[OH:1][C@@H:2]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:23]2[C:22](=[O:28])[CH2:21][C@@:20]2([CH3:29])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:19])[CH2:13][CH:14](OC)[O:15]C)[CH2:3]1>C(O)(=O)C.O>[CH:14]([CH2:13][C:12](=[O:19])[C@@H:11]1[C@:20]2([CH3:29])[C@H:8]([C@H:7]3[C@H:23]([C:22](=[O:28])[CH2:21]2)[C@:24]2([CH3:27])[C@H:4]([CH2:3][C@H:2]([OH:1])[CH2:26][CH2:25]2)[CH2:5][CH2:6]3)[CH2:9][CH2:10]1)=[O:15]

Participants

4

Reactant 1

HCID 86734295HCID 86734295, compound

Product 1

HCID 8673429421-Formyl-3alpha-hydroxy-5alpha-pregnane-11,20-dioneYield 49.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of 3α-hydroxy-21-dimethoxymethyl-5α-pregnane-11,20-dione (900 mg.) in glacial acetic acid (13 ml) and water (1.3 ml) was stirred at 75° C for 6 hours, then poured into a mixture of ice and water. The product was collected, washed with water and dried in vacuo to give title compound (395 mg), [α]D + 100.5° (c, 0.4), λmax. 268 nm (ε 6,325).

Workup

  1. customThe product was collected
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-f311816e0b2f450b9974ec227fe8794c
Source dataset
uspto-grants-1976_12
Patent number
US03998829

Reaction notes

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