Diisopropylethylamine → {1-[2-((R)-3-Hydroxy-piperidin-1-yl)-ethyl]-piperidin-4-yl}-carbamic acid tert-butyl ester

HRID 2267683Notes

Reaction equation

HRID 2267683 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15]O)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].Cl.[OH:19][C@@H:20]1[CH2:25][CH2:24][CH2:23][NH:22][CH2:21]1.CCN(C(C)C)C(C)C.[I-].C(C[P+](C)(C)C)#N>>[C:1]([O:5][C:6](=[O:17])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:22]2[CH2:23][CH2:24][CH2:25][C@@H:20]([OH:19])[CH2:21]2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 2759333(3R)-piperidin-3-ol hydrochlorideHCID 10514344(Cyanomethyl)trimethylphosphanium iodideHCID 45076484[1-(2-Hydroxy-ethyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

Product 1

HCID 66842084{1-[2-((R)-3-Hydroxy-piperidin-1-yl)-ethyl]-piperidin-4-yl}-carbamic acid tert-butyl ester

Procedure

It is prepared analogously to 9 starting from tert-butyl ester 8 (3.52 g, 14.41 mmol), (R)-3-hydroxy-piperidine hydrochloride (2.18 g, 15.85 mmol), DIEA (5.6 ml, 33.14 mmol) and cyanomethyl-trimethyl-phosphonium iodide (4.2 g, 17.29 mmol).

Sources & evidence

ORD record
ord-8697a0c4f753466a91d6772a8f31388b
Source dataset
uspto-grants-2010_12
Patent number
US07858781B2

Reaction notes

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