t-Butyl 4-phenyl-2-butenoate → (3R,alphaS)-t-Butyl 3-(alpha-methylbenzylamino)-4-methylpentanoate

HRID 1637043Notes

Reaction equation

HRID 1637043 reaction equation
C([N:4]([C@@H:17]([CH3:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C@@H:5]([CH:14]([CH3:16])[CH3:15])[CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])C=C.C(N([C@@H](C)C1C=CC=CC=1)[C@@H](C=CC1C=CC=CC=1)CC(OC(C)(C)C)=O)C=C.C1(CC=CC(OC(C)(C)C)=O)C=CC=CC=1>C(Cl)(Cl)Cl>[CH3:24][C@H:17]([NH:4][C@@H:5]([CH:14]([CH3:16])[CH3:15])[CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 53401901t-Butyl 4-phenyl-2-butenoateHCID 86755224(3R,alphaS)-t-Butyl 3-(N-allyl-alpha-methylbenzylamino)-5-phenyl-4-pentenoate3×HCID 86755234(3R,alphaS)-t-Butyl 3-(N-allyl-alpha-methylbenzylamino)-4-methylpentanoate

Product 1

HCID 86755233(3R,alphaS)-t-Butyl 3-(alpha-methylbenzylamino)-4-methylpentanoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

The title compound (34) was prepared from compound (16) of Example 6 using the above-described procedure. [α]D21 -52.7 (c 1.57, CHCl3); νmax (CHCl3)/cm-1 1724 s (C=O); δH (300 Hz; CDCl3) 7.38-7.21 (5H, m, Ph), 3.88 (1H, q, J=6.5, PhCHCH3), 2.60 (1H, m, NCHCH2), 2.38, 2.27 (2H, ABX system, JAB =14.4, JAX =5.4, JBX =6.2, CH2CO), 1.68 (1H, m, (CH3)2CH), 1.47 (9H, s, (CH3)3C), 1.33) (3H, d, J=6.5, PhCHCH3), 0.89 (3H, d, J=6.8, (CH3)2CH), 0.81 (3H, d, J=6.8, (CH3)2CH); δC (50 MHz; CDCl3) 172.67 (C=O), 146.58 (Ph:Cipso), 128.42, 127.12 (Ph:Cortho, Cmeta), 126.95 (Ph:Cpara), 80.19 (C(CH3)3), 57.82, 55.37 (CHN), 36.81 (CH2CO), 31.14 ((CH3)2CH), 28.03 (C(CH3)3), 24.76 (NCHCH3), 18.78, 18.32 ((CH3)2CH); m/z (CI) 292 (MH+, 100%), 236 (20), 192 (20), 176 (17), 105 (20); (Found: C, 74.07; H, 10.31; N, 4.58. C18H29NO2 requires C, 74.18; H, 10.03; N, 4.81%).

Sources & evidence

ORD record
ord-3b731dca36e74b6c9be6777001e27a35
Source dataset
uspto-grants-2000_03
Patent number
US06037498

Reaction notes

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