Pyrrolidine → HCID 9979015, compound

HRID 895846Notes

Reaction equation

HRID 895846 reaction equation
[OH:1][C@H:2]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[CH:4]([CH2:5][CH2:6][C:7]3[C:8]4[C@:16]([CH3:24])([CH2:17][CH2:18][C:19]=32)[C@@H:11]([C@H:12]([CH3:15])[CH:13]=O)[CH2:10][CH:9]=4)[C:3]1([CH3:26])[CH3:25].[NH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[N:27]1([CH2:13][C@H:12]([C@@H:11]2[C@:16]3([CH3:24])[C:8]([C:7]4[CH2:6][CH2:5][C@@H:4]5[C@:20]([C:19]=4[CH2:18][CH2:17]3)([CH3:23])[CH2:21][CH2:22][C@H:2]([OH:1])[C:3]5([CH3:26])[CH3:25])=[CH:9][CH2:10]2)[CH3:15])[CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

4

Reactant 3

HCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 11772697HCID 11772697, compound

Product 1

HCID 9979015HCID 9979015, compound

Procedure

(20S)-3β-hydroxy-4,4,20-trimethyl-pregna-8,14-dien-21-al was treated with pyrrolidin and sodium tris(acetoxy)borohydride as described in Example 1h). (20S)-20-[(pyrrolidin-1-yl)methyl]-4,4-dimethyl-5α-pregna-8,14-dien-3β-ol was isolated as a white solid.

Sources & evidence

ORD record
ord-bd2149760c94489f886f12c082d61425
Source dataset
uspto-grants-2005_07
Patent number
US06916921B2

Reaction notes

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