3-Methylpyrrolidin-3-ol → HCID 89538970, compound

HRID 2179111Notes

Reaction equation

HRID 2179111 reaction equation
[CH2:1]([N:8]1[C:12]2[N:13]=[C:14]([C:23]([CH3:26])([CH3:25])[CH3:24])[N:15]=[C:16]([N:17]3[CH2:21][CH2:20][C@@H:19]([OH:22])[CH2:18]3)[C:11]=2[N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:27]([N:34]1[C:38]2[N:39]=[C:40]([C:44]([CH3:47])([CH3:46])[CH3:45])[N:41]=[C:42](Cl)[C:37]=2[N:36]=[N:35]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[CH3:48][C:49]1([OH:54])[CH2:53][CH2:52][NH:51][CH2:50]1>>[CH2:1]([N:8]1[C:12]2[N:13]=[C:14]([C:23]([CH3:26])([CH3:25])[CH3:24])[N:15]=[C:16]([N:17]3[CH2:21][CH2:20][C:19]([CH3:27])([OH:22])[CH2:18]3)[C:11]=2[N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:27]([N:34]1[C:38]2[N:39]=[C:40]([C:44]([CH3:47])([CH3:46])[CH3:45])[N:41]=[C:42]([N:51]3[CH2:52][CH2:53][C@:49]([CH3:48])([OH:54])[CH2:50]3)[C:37]=2[N:36]=[N:35]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[CH2:1]([N:8]1[C:12]2[N:13]=[C:14]([C:23]([CH3:26])([CH3:25])[CH3:24])[N:15]=[C:16]([N:17]3[CH2:21][CH2:20][C@@:19]([CH3:27])([OH:22])[CH2:18]3)[C:11]=2[N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 145784583-Methylpyrrolidin-3-olHCID 866833853-Benzyl-5-tert-butyl-7-chloro-triazolo[4,5-d]pyrimidineHCID 86683386(R)-1-(3-Benzyl-5-tert-butyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl)-pyrrolidin-3-ol

Product 3

HCID 89538970HCID 89538970, compoundHCID 89538973HCID 89538973, compoundHCID 89539042(R)-1-(3-benzyl-5-tert-butyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl)-3-methylpyrrolidin-3-ol

Procedure

In analogy to the procedure described for the synthesis of (R)-1-(3-Benzyl-5-tert-butyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl)-pyrrolidin-3-ol (example 113, a) the title compound was prepared from 3-benzyl-5-tert-butyl-7-chloro-triazolo[4,5-d]pyrimidine and 3-Methyl-pyrrolidin-3-ol and subjected to separation by chiral HPLC to yield (S)-1-(3-benzyl-5-tert-butyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl)-3-methylpyrrolidin-3-ol and (R)-1-(3-benzyl-5-tert-butyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl)-3-methylpyrrolidin-3-ol. The enantiopure intermediates where isolated with 39% and 36% yield.

Workup

  1. customsubjected to separation by chiral HPLC

Sources & evidence

ORD record
ord-a90d477f97e24abdaa46b49ce2f605e9
Source dataset
uspto-grants-2015_06
Patent number
US09067943B2

Reaction notes

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