3,3-Dimethylbutanal → HCID 70480169, compound

HRID 615200Notes

Reaction equation

HRID 615200 reaction equation
C([BH3-])#N.[Na+].[NH2:5][C@@H:6]1[CH2:23][C@@:21]2([CH3:22])[C@@H:17]([CH2:18][CH2:19][C@@H:20]2[C:24]([O:26][CH3:27])=[O:25])[C@H:16]2[C@H:7]1[C@:8]1([CH3:30])[C@@H:13]([CH2:14][CH2:15]2)[CH2:12][C@H:11]([OH:28])[C@@H:10]([OH:29])[CH2:9]1.[CH3:31][C:32]([CH3:37])([CH3:36])[CH2:33][CH:34]=O>C(O)C.C(=O)([O-])O.[Na+]>[CH3:31][C:32]([CH3:37])([CH3:36])[CH2:33][CH2:34][NH:5][C@@H:6]1[CH2:23][C@@:21]2([CH3:22])[C@@H:17]([CH2:18][CH2:19][C@@H:20]2[C:24]([O:26][CH3:27])=[O:25])[C@H:16]2[C@H:7]1[C@:8]1([CH3:30])[C@@H:13]([CH2:14][CH2:15]2)[CH2:12][C@H:11]([OH:28])[C@@H:10]([OH:29])[CH2:9]1

Participants

6

Reactant 3

HCID 763353,3-DimethylbutanalHCID 5003444Sodium cyanoborohydrideHCID 70479964HCID 70479964, compound

Product 1

HCID 70480169HCID 70480169, compoundYield 126.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Sodium cyanoborohydride (1.5 g) was added to a mixture of methyl 11α-amino-2β,3α-dihydroxy-5α-androstane-17β-carboxylate (760 mg) and 3,3-dimethyl-butyraldehyde (700 mg) in ethanol (30 ml). The mixture was stirred for 18 h, diluted with 5% sodium hydrogen carbonate solution and extracted with ethyl acetate (3×). The extract was washed with water, dried and evaporated to give a foam (1.18 g) which was purified by preparation t.l.c. in ethyl acetate/0.88 ammonia (50:1) to give the title compound (565 mg) as a foam, [α]D +22.1°, νmax 1725 cm-1.

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. washThe extract was washed with water
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-ed1cb288cbbd4902857d5ff0073c243d
Source dataset
uspto-grants-1985_02
Patent number
US04497805

Reaction notes

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