Phosphorus oxychloride → 3-(5-Phenyl-oxazol-2-yl)-1,2,3,4-tetrahydro-isoquinoline

HRID 1823930Notes

Reaction equation

HRID 1823930 reaction equation
C(OC([N:11]1[CH:20]([C:21](=[O:32])[NH:22][CH2:23][C:24](=O)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12]1)=O)C1C=CC=CC=1.C(OC(N1C(C(=O)NCC(=O)C2C=CC=CC=2)CC2C(=CC=CC=2)C1)=O)(C)(C)C.O=P(Cl)(Cl)Cl>>[C:25]1([C:24]2[O:32][C:21]([CH:20]3[CH2:19][C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH2:12][NH:11]3)=[N:22][CH:23]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 235707253-(2-oxo-2-phenyl-ethylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert butyl esterHCID 668926493-(2-oxo-2-phenyl-ethylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester

Product 1

HCID 221476803-(5-Phenyl-oxazol-2-yl)-1,2,3,4-tetrahydro-isoquinoline

Procedure

Dehydration of 3-(2-oxo-2-phenyl-ethylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester (prepared in a similar manner as 3-(2-oxo-2-phenyl-ethylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert butyl ester of Example 1) with POCl3 yields the following intermediate compound:

Workup

  1. customyields the following intermediate compound

Sources & evidence

ORD record
ord-8e945a81d1f74afca962ca54c293d4a7
Source dataset
uspto-grants-2006_05
Patent number
US07041681B2

Reaction notes

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