Monobasic potassium phosphate → HCID 57069603, compound

HRID 1613985Notes

Reaction equation

HRID 1613985 reaction equation
[BH4-].[Na+].[C:3]([C:5](=[C:11]1[C@:28]2([CH3:29])[C@H:14]([C@H:15]3[C@:25]([OH:30])([CH2:26][CH2:27]2)[C@:23]2([CH3:24])[C:18]([CH2:19][C:20]4([O:34][CH2:33][CH2:32][O:31]4)[CH2:21][CH2:22]2)=[CH:17][CH2:16]3)[CH2:13][CH2:12]1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])#[N:4].[H-].[Al+3].[Li+].[H-].[H-].[H-].P([O-])(O)(O)=O.[K+]>O1CCCC1>[C:3]([CH:5]([C@@H:11]1[C@:28]2([CH3:29])[C@H:14]([C@H:15]3[C@:25]([OH:30])([CH2:26][CH2:27]2)[C@:23]2([CH3:24])[C:18]([CH2:19][C:20]4([O:31][CH2:32][CH2:33][O:34]4)[CH2:21][CH2:22]2)=[CH:17][CH2:16]3)[CH2:13][CH2:12]1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])#[N:4]

Participants

6

Reactant 4

HCID 516951Monobasic potassium phosphateHCID 4311764Sodium borohydrideHCID 21226445Aluminium lithium hydrideHCID 57234291HCID 57234291, compound

Product 1

HCID 57069603HCID 57069603, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (0.70 g) was added in small portions to a stirred solution of ethyl 20-cyano-3,3-ethylenedioxy-9α-hydroxypregna-5,17(20)-dien-21-oate (1.76 g) in dry tetrahydrofuran (15 ml). After stirring at room temperature for 5 hours, lithium aluminium hydride (0.12 g) was added in 3 portions and stirring was continued for 3 hours. Aqueous saturated potassium dihydrogen phosphate (15 ml) was added and the mixture was extracted with ethyl acetate. The organic extract was washed with aqueous sodium bicarbonate, then washed twice with water, dried and concentrated under reduced pressure to afford 0.82 g of the title compound.

Workup

  1. stirringstirring
  2. waitwas continued for 3 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with aqueous sodium bicarbonate
  6. washwashed twice with water
  7. customdried
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d275f9fbd9634312b0a755fc9ece0224
Source dataset
uspto-grants-1993_03
Patent number
US05194602

Reaction notes

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