Benzylamine → HCID 10791708, compound

HRID 1492809Notes

Reaction equation

[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(=O)[C:13]([C@@H:15]1[CH2:19][C@@H:18]([O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH2:17][N:16]1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=C)C.CCCCCC.[C:42]([O:45][CH2:46][CH3:47])(=[O:44])[CH3:43]>>[CH2:46]([O:45][C:42](=[O:44])[CH2:43][CH:13]([NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@@H:15]1[CH2:19][C@@H:18]([O:20][Si:21]([C:24]([CH3:25])([CH3:26])[CH3:27])([CH3:23])[CH3:22])[CH2:17][N:16]1[C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[CH3:47]

Participants

Reactant 3

HCID 7504Benzylamine

HCID 21226206Ethyl acetate hexane

HCID 67749947HCID 67749947, compound

Product 1

HCID 10791708HCID 10791708, compoundYield 70.5%

Procedure

Benzylamine (1.2 ml, 11 mmol) was added to [(2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldimethylsiloxypyrrolidin-2-yl]acrylic acid ethyl ester (2.18 g, 5.46 mmol, compound of Reference Example 1-4). The mixture was stirred at room temperature for five days. Then, this mixture was subjected to silica gel column chromatography (Wakogel™ C-300, hexane-ethyl acetate 3:1) to obtain 3-benzylamino-3-[(2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldimethylsiloxypyrrolidin-2-yl]propionic acid ethyl ester (1.95 g, yield: 70.5%). NMR(CDCl3) δ: 0.05(6H,s),0.86(9H,s),1.24(3H,t,J=8Hz),1.44(9H,s), 1.90(1H,m),2.35(2H,m),3.26(1H,m),3.89 and 3.96 (2H,ABq,J=8Hz),4.14(2H,q,J=8Hz),4.39(1H,m), 7.31(5H,m) ##STR1247##

Sources & evidence

ORD record: ord-8794e33fdcbc488f9e6392bd05632488
Source dataset: uspto-grants-1994_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05374720

Reaction notes

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