N-(9-Fluorenylmethoxycarbonyloxy)succinimide → n-[(r)-2-[(9h-Fluoren-9-ylmethoxycarbonyl)(1-isopropyl-piperidin-4-ylmethyl)amino]-1-phenylethyl]carbamic acid tert-butyl ester

HRID 32464

Reaction equation

HRID 32464 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C@H:8]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:9][NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([CH:18]([CH3:20])[CH3:19])[CH2:14][CH2:13]1)([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([O:35][C:36]([O:38][CH2:39][CH:40]2[C:52]3[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=3)[C:46]3[C:41]2=[CH:42][CH:43]=[CH:44][CH:45]=3)=O)C(=O)C1>>[C:1]([O:5][C:6](=[O:27])[NH:7][C@H:8]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:9][N:10]([C:36]([O:38][CH2:39][CH:40]1[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][C:46]=2[C:47]2[C:52]1=[CH:51][CH:50]=[CH:49][CH:48]=2)=[O:35])[CH2:11][CH:12]1[CH2:13][CH2:14][N:15]([CH:18]([CH3:19])[CH3:20])[CH2:16][CH2:17]1)([CH3:3])([CH3:4])[CH3:2]

Participants

3

Reactant 2

HCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 69307988N-[(R)-2-[(1-Isopropylpiperidin-4-ylmethyl)amino]-1-phenyl-ethyl]carbamic acid tert-butyl ester

Product 1

HCID 69309681n-[(r)-2-[(9h-Fluoren-9-ylmethoxycarbonyl)(1-isopropyl-piperidin-4-ylmethyl)amino]-1-phenylethyl]carbamic acid tert-butyl esterYield 113.5%

Procedure

Using coupling method B, N-[(R)-2-[(1-isopropylpiperidin-4-ylmethyl)amino]-1-phenylethyl]carbamic acid tert-butyl ester (1.1 g, 2.8 mmol) and 9-fluorenylmethyl N-succinimidyl carbonate (Fmoc-OSu, 962 mg, 2.9 mmol) afforded 1.9 g of the title compound as a crude residue, that was used without further purification.

Sources & evidence

ORD record
ord-e4a11d44c2f74fedb928844e4d48c9a0
Source dataset
uspto-grants-2008_09
Patent number
US07427632B2

Linked notes

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