Pyrrolidine → (S)-3-(Pyrrolidin-1-ylmethyl)-1,2,3,4-tetrahydroisoquinoline

HRID 528872Notes

Reaction equation

HRID 528872 reaction equation
[CH:1]([C@@H:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][N:4]1C(OC(C)(C)C)=O)=O.[NH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1>>[N:20]1([CH2:1][C@@H:3]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5][NH:4]2)[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 22861260(S)-tert-Butyl 3-formyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 10798781(S)-3-(Pyrrolidin-1-ylmethyl)-1,2,3,4-tetrahydroisoquinoline

Procedure

Following a procedure analogous to that for the synthesis of Example 107, (S)-tert-butyl 3-formyl-3,4-dihydroisoquinoline-2(1H)-carboxylate (57 mg, 0.22 mmol) and pyrrolidine (16 mg, 0.22 mmol) provided a crude oil which was used without purification in preparation of Example 111. MS(ESI+) m/z 217.1 (M+H)+.

Workup

  1. customprovided a crude oil which
  2. customwas used without purification in preparation of Example 111

Sources & evidence

ORD record
ord-5e5f249eb5cc43f09780b11b0006243a
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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