3,3-Dimethylpiperidine → HCID 60017453, compound

HRID 895842Notes

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].[CH3:27][C:28]1([CH3:34])[CH2:33][CH2:32][CH2:31][NH:30][CH2:29]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH3:27][C:28]1([CH3:34])[CH2:33][CH2:32][CH2:31][N:30]([CH2:15][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)[CH3:13])[CH2:29]1

Participants

Reactant 3

HCID 709423,3-Dimethylpiperidine

HCID 5049666Sodium triacetoxyborohydride

HCID 11772697HCID 11772697, compound

Product 1

HCID 60017453HCID 60017453, compound

Procedure

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

Sources & evidence

ORD record: ord-ea808e9914a84268b065d78c2db36dd5
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06916921B2

Reaction notes

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