(4S)-4-(Aminomethyl)-1-(tert-butoxycarbonyl)-L-proline → 1-(1,1-Dimethylethyl) (2S,4R)-4-(aminomethyl)-1,2-pyrrolidinedicarboxylate

HRID 893059Notes

Reaction equation

HRID 893059 reaction equation
C([O:8][C:9](=[O:24])[C@@H:10]1[CH2:14][C@@H:13]([C:15]#[N:16])[CH2:12][N:11]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])C1C=CC=CC=1.C(OC(N1C[C@H](CN)C[C@H]1C(O)=O)=O)(C)(C)C>>[C:20]([O:19][C:17]([N:11]1[CH2:12][C@@H:13]([CH2:15][NH2:16])[CH2:14][C@H:10]1[C:9]([OH:24])=[O:8])=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

3

Reactant 2

HCID 14842646(4S)-4-(Aminomethyl)-1-(tert-butoxycarbonyl)-L-prolineHCID 14842663HCID 14842663, compound

Product 1

HCID 148426491-(1,1-Dimethylethyl) (2S,4R)-4-(aminomethyl)-1,2-pyrrolidinedicarboxylateYield 67%

Procedure

Cyano acid benzyl acid ester 36 (3.0 g, 9.1 mmol) was hydrogenated as for the synthesis of 12, and the product was crystallized from water/ethanol/ether to give 1.5 g (67% yield), m.p.=230°-231° C. 1H NMR (D2O) δ1.41/1.46 (2s, 9H), 2.11 (m, 1H), 2.60 (m, 1H), 3.12 (m, 2H), 3.73 (m, 1H), 4.17 (dd, J=9.0/3.9,1H).

Workup

  1. customthe product was crystallized from water/ethanol/ether
  2. customto give 1.5 g (67% yield), m.p.=230°-231° C

Sources & evidence

ORD record
ord-aa7c69cc12b047a28a1b9a5c6641afe6
Source dataset
uspto-grants-1992_06
Patent number
US05120859

Reaction notes

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