tert-Butyl ((1S,3S)-3-hydroxycyclopentyl)carbamate → cis-3-(2,5-Dimethyl-benzoimidazol-1-yl)-cyclopentylamine

HRID 1993873Notes

Reaction equation

HRID 1993873 reaction equation
C(OC(=O)N[C@H]1CC[C@H](O)C1)(C)(C)C.C(OC(=O)N[C@H]1CC[C@@H](N)C1)(C)(C)C.C(OC(=O)[NH:35][C@H:36]1[CH2:40][CH2:39][C@@H:38]([N:41]2[C:45]3[CH:46]=[CH:47][C:48]([CH3:50])=[CH:49][C:44]=3[N:43]=[C:42]2[CH3:51])[CH2:37]1)(C)(C)C.CC1N([C@H]2CC[C@H](N)C2)C2C=CC(C)=CC=2N=1>>[CH3:51][C:42]1[N:41]([C@@H:38]2[CH2:39][CH2:40][C@H:36]([NH2:35])[CH2:37]2)[C:45]2[CH:46]=[CH:47][C:48]([CH3:50])=[CH:49][C:44]=2[N:43]=1

Participants

5

Reactant 4

HCID 21637082tert-Butyl ((1S,3S)-3-hydroxycyclopentyl)carbamateHCID 517769401,1-Dimethylethyl N-[(1S,3R)-3-aminocyclopentyl]carbamateHCID 66877067trans-3-(2,5-Dimethyl-benzoimidazol-1-yl)-cyclopentylamineHCID 66878048cis-[3-(2,5-Dimethyl-benzoimidazol-1-yl)-cyclopentyl]-carbamic acid tert-butyl ester

Product 1

HCID 59135473cis-3-(2,5-Dimethyl-benzoimidazol-1-yl)-cyclopentylamine

Procedure

The trans-(3-hydroxy-cyclopentyl)-carbamic acid tert-butyl ester was converted to cis-(3-amino-cyclopentyl)-carbamic acid tert-butyl ester using the same method described previously. The resulting compound was further converted to cis-[3-(2,5-dimethyl-benzoimidazol-1-yl)-cyclopentyl]-carbamic acid tert-butyl ester using the same method described in the preparation of the hydrochloride salt of trans-3-(2,5-dimethyl-benzoimidazol-1-yl)-cyclopentylamine. After the acid cleavage of the carbamic acid tert-butyl ester and base extraction, cis-3-(2,5-dimethyl-benzoimidazol-1-yl)-cyclopentylamine was obtained as pale brown oil. LR-MS calcd for C14H19N3 (m/e) 229.1579, obsd 230.2 (M+H).

Workup

  1. extractionAfter the acid cleavage of the carbamic acid tert-butyl ester and base extraction

Sources & evidence

ORD record
ord-80bcdaab5f664838bb6e26314de6bc88
Source dataset
uspto-grants-2010_01
Patent number
US07652053B2

Reaction notes

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