Nitroethane → tert-Butyl 4-(1-hydroxy-2-nitropropyl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate

HRID 528967Notes

Reaction equation

HRID 528967 reaction equation
[CH:1]([C:3]1[CH:15]=[CH:14][C:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[CH:5][C:4]=1[C:16]([N:18]1[CH2:27][CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19]1)=[O:17])=[O:2].[N+:28]([CH2:31][CH3:32])([O-:30])=[O:29]>>[OH:2][CH:1]([C:3]1[CH:15]=[CH:14][C:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[CH:5][C:4]=1[C:16]([N:18]1[CH2:27][CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19]1)=[O:17])[CH:31]([N+:28]([O-:30])=[O:29])[CH3:32]

Participants

3

Reactant 2

HCID 6587NitroethaneHCID 86718914tert-Butyl 4-formyl-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate

Product 1

HCID 71062233tert-Butyl 4-(1-hydroxy-2-nitropropyl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 223C, tert-butyl 4-formyl-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate (59 mg, 0.16 mmol) and nitroethane (0.023 mL, 0.32 mmol) were converted to the title compound as a crude brown oil (1:1 mixture of diastereomers by LC-MS) which was used directly without further purification. MS(ESI+) m/z 441.3 (M+H)+.

Sources & evidence

ORD record
ord-501c2bbeafae4c80943b05d835ed6a45
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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