Morpholine → HCID 86734301, compound

HRID 1973732Notes

Reaction equation

HRID 1973732 reaction equation
[OH:1][C@@H:2]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:24]2[C:23](=[O:29])[CH2:22][C@@:21]2([CH3:30])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:20])[CH2:13][CH2:14][O:15][C:16](=[O:19])[CH2:17]I)[CH2:3]1.[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>ClCCl>[OH:1][C@@H:2]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:24]2[C:23](=[O:29])[CH2:22][C@@:21]2([CH3:30])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:20])[CH2:13][CH2:14][O:15][C:16](=[O:19])[CH2:17][N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)[CH2:3]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 86734302HCID 86734302, compound

Product 1

HCID 86734301HCID 86734301, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3α-Hydroxy-21-iodoacetoxymethyl-5α-pregnane-11,20-dione (230 mg) in dry dichloromethane (25 ml) was treated with morpholine (1.0 ml) and the solution was stirred at room temperature for 30 minutes. The solution was diluted with dichloromethane, washed twice with water, dried over sodium sulphate and evaporated to a colourless gum (230 mg) which was purified by preparative t.l.c. in acetone/petrol 1:1. The main band was separated to give title compound (172 mg) as a white foam, [α]D + 79° (c 0.68).

Workup

  1. washwashed twice with water
  2. dry with materialdried over sodium sulphate
  3. customevaporated to a colourless gum (230 mg) which
  4. customwas purified by preparative t.l.c
  5. customThe main band was separated

Sources & evidence

ORD record
ord-3210e731327d4eb8901a293f8ee24c1e
Source dataset
uspto-grants-1976_12
Patent number
US03998829

Reaction notes

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