Methoxymethyl-triphenylphosphonium chloride → N-benzyloxycarbonyl-3(R,S)-(1-methoxyethen-2-yl)-1,2,3,4-tetrahydroquinoline

HRID 863320Notes

Reaction equation

HRID 863320 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.[Cl-].[CH3:24][O:25][CH2:26][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:24][O:25][CH3:26])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 19697710N-benzyloxycarbonyl-3(R,S)-formyl-1,2,3,4-tetrahydroquinolineHCID 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 57219624N-benzyloxycarbonyl-3(R,S)-(1-methoxyethen-2-yl)-1,2,3,4-tetrahydroquinoline

Procedure

The title compound is prepared in a manner analogous to that described in Example 137b) starting from 4.8 g of N-benzyloxycarbonyl-3(R,S)-formyl-1,2,3,4-tetrahydroquinoline, 7.2 g of methoxymethyl-triphenylphosphonium chloride and 5.4 g of sodium-bis(trimethylsilyl)amide: Rf (A)=0.67.

Sources & evidence

ORD record
ord-2602d2bcabd84ae2bd16b3016c1536b5
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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