Tetrahydrofuran → HCID 67744901, compound

HRID 1885335Notes

Reaction equation

HRID 1885335 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[N:5]([C:8]1[C:28](=[O:29])[CH2:27][CH2:26][C@@:25]2([CH3:30])[C:9]=1[CH2:10][CH2:11][C@@H:12]1[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:31])[C@H:13]1[CH2:14][CH2:15][C@@H:16]2[C@H:17]([CH3:20])[CH2:18][OH:19])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1>O>[C:1]([OH:4])(=[O:3])[CH3:2].[NH2:5][C:8]1[C:28](=[O:29])[CH2:27][CH2:26][C@@:25]2([CH3:30])[C:9]=1[CH2:10][CH2:11][C@@H:12]1[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:31])[C@H:13]1[CH2:14][CH2:15][C@@H:16]2[C@H:17]([CH3:20])[CH2:18][OH:19]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 86745919HCID 86745919, compound

Product 1

HCID 67744901HCID 67744901, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of (20S)-4-azido-21-hydroxy-20-methylpregn-4-en-3-one acetate (1.4 g, 3.39 mmole), triphenyl-phosphine (1.08 g), tetrahydrofuran (25 mL) and water (7 mL) was heated at reflux temperature under argon for 18 hours. The solvents were removed from the cooled reaction and the residue was purified by flash chromatography to give (20S)-4-amino-21-hydroxy-20-methylpregn-4-en-3-one acetate (1.1 g, 84%). IR 3470, 3366, 1732, 1674, 1618, 1584, 1254 cm-1 ; MS (CI) 388 (100%, M+1), 328 (70% M+1-AcOH); 1H NMR (CDCl3) δ 0.72 (3H, s, C18 -Me), 1.00 (d, C22 -Me), 1.14 (s, C19 -Me), 2.04 (s, Ac-Me), 3.43 (2H, v br, NH2), 3.76 (1H, dd, 1/2 C21 -CH2), 4.07 (1H, dd, 1/2 C21 -CH2). This compound has the following structure: ##STR5##

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature under argon for 18 hours
  3. customThe solvents were removed from the cooled reaction
  4. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-5a8f362e84cb4f80bc4eac672998637a
Source dataset
uspto-grants-1992_09
Patent number
US05143909

Reaction notes

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