Sodium bis(trimethylsilyl)amide → N-Benzyloxycarbonyl-3(R,S)-(1-methoxyprop-2-en-3-yl)-1,2,3,4-tetrahydroquinoline

HRID 863324Notes

Reaction equation

HRID 863324 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH:13]([CH:21]=O)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br-].[CH3:24][O:25][CH2:26][CH2:27][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C(NC(=O)[C@H](C)C[C@H](O)[C@@H](NC(OC(C)(C)C)=O)CC(C)(C)CC(N1C2C(=CC=CC=2)CC(COCC=C)C1)=O)CCC>>[CH2:1]([O:8][C:9]([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH:13]([CH:21]=[CH:27][CH2:26][O:25][CH3:24])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 19697710N-benzyloxycarbonyl-3(R,S)-formyl-1,2,3,4-tetrahydroquinolineHCID 22377376(2-Methoxy-ethyl)-triphenyl-phosphonium, bromideHCID 1317205295(S)-tert-butoxycarbonylamino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[3(R,S)-allyloxymethyl-1,2,3,4-tetrahydroquinolin-1-ylcarbonyl]-octanoic acid (N-butyl)amide

Product 1

HCID 56984159N-Benzyloxycarbonyl-3(R,S)-(1-methoxyprop-2-en-3-yl)-1,2,3,4-tetrahydroquinoline

Procedure

The title compound is prepared in a manner analogous to that described in Example 137b) starting from 1.50 g of N-benzyloxycarbonyl-3(R,S)-formyl-1,2,3,4-tetrahydroquinoline, 3.1 g of methoxyethyl-triphenylphosphonium bromide and 2.0 g of sodium bis(trimethylsilyl)amide: Rf (A)=0.55.

Sources & evidence

ORD record
ord-e8d60ba8f22e41d5a245c58990c2dace
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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