Morpholine → 2beta-(4-Morpholinyl)-16beta-(1-pyrrolidinyl)-5alpha-androstane-3alpha,17beta-diol

HRID 2099862

Reaction equation

HRID 2099862 reaction equation
[O:1]1[C@H:3]2[CH2:4][C@H:5]3[C@:18]([CH3:20])([CH2:19][C@@H:2]12)[C@@H:17]1[C@H:8]([C@H:9]2[C@@:13]([CH2:15][CH2:16]1)([CH3:14])[C@@H:12]([OH:21])[C@@H:11]([N:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)[CH2:10]2)[CH2:7][CH2:6]3.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>O>[N:27]1([C@H:2]2[CH2:19][C@@:18]3([CH3:20])[C@@H:5]([CH2:6][CH2:7][C@@H:8]4[C@@H:17]3[CH2:16][CH2:15][C@@:13]3([CH3:14])[C@H:9]4[CH2:10][C@H:11]([N:22]4[CH2:26][CH2:25][CH2:24][CH2:23]4)[C@@H:12]3[OH:21])[CH2:4][C@@H:3]2[OH:1])[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 160638722Alpha,3alpha-epoxy-16beta-(1-pyrrolidinyl)-5alpha-androstan-17beta-OL

Product 1

HCID 160638732beta-(4-Morpholinyl)-16beta-(1-pyrrolidinyl)-5alpha-androstane-3alpha,17beta-diol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

wherein R3 is C, N—CH3 or a direct C—C bond. The yield is modest (around 60% w/w yield). The patent discloses the reaction of 2α,3α-epoxy-16β-(1-pyrrolidinyl)-5α-androstan-17β-ol with morpholine in the presence of water to yield 2β-(4-morpholinyl)-16β-(1-pyrrolidinyl)-5α-androstan-3α,17β-diol. The step is conducted for a reaction time of three days after which the solvents are removed by evaporation and the final product is crystallized from acetone followed by further recrystallization from methanol.

Workup

  1. custom(around 60% w/w yield)

Sources & evidence

ORD record
ord-d51aaa9c1dcc4bb6a733027161506b49
Source dataset
uspto-grants-2009_08
Patent number
US07569687B2

Linked notes

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