(3R)-1-benzylpyrrolidin-3-amine → HCID 70032808, compound

HRID 1060609Notes

Reaction equation

[CH2:1]([NH:8][C:9]([CH:11]1[CH2:23][N:21]2[C:22]3[CH:14]([CH:15]([NH:24][C:25](=[O:38])[CH:26]([CH2:34][CH:35]([CH3:37])[CH3:36])[CH:27]([CH2:31][CH2:32][CH3:33])[C:28]([NH2:30])=[O:29])[CH2:16][CH2:17][C:18]=3[CH:19]=[CH:20]2)[C:13](=[O:39])[CH2:12]1)=[O:10])C1C=CC=CC=1.N[C@@H:41]1C[CH2:44][N:43]([CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH2:42]1>>[CH2:46]([N:43]1[CH2:42][CH2:41][CH:1]([NH:8][C:9]([CH:11]2[CH2:23][N:21]3[C:22]4[CH:14]([CH:15]([NH:24][C:25](=[O:38])[CH:26]([CH2:34][CH:35]([CH3:37])[CH3:36])[CH:27]([CH2:31][CH2:32][CH3:33])[C:28]([NH2:30])=[O:29])[CH2:16][CH2:17][C:18]=4[CH:19]=[CH:20]3)[C:13](=[O:39])[CH2:12]2)=[O:10])[CH2:44]1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

Reactant 2

HCID 1519354(3R)-1-benzylpyrrolidin-3-amine

HCID 70033043HCID 70033043, compound

Product 1

HCID 70032808HCID 70032808, compoundYield 30%

Procedure

The compound of Example 3b was synthesized in a manner similar to the synthesis of the compound of Example 3a, but using (R)-3-amino-1-benzylpyrrolidine as the amine in the last step. Cleavage of 100 mg of functionalized resin (0.52 mmol/g) and purification by RP-HPLC provided 10.5 mg (30%) of the title compound as a white powder. MS (M+H)+=602.5.

Workup

customCleavage of 100 mg of functionalized resin (0.52 mmol/g) and purification by RP-HPLC

Sources & evidence

ORD record: ord-047740b1add946fb863d0532f9321765
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06525044B2

Reaction notes

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