Piperidin-4-ol → (S)-1-((1,2,3,4-Tetrahydroisoquinolin-3-yl)methyl)piperidin-4-ol

HRID 528871Notes

Reaction equation

HRID 528871 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[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22][CH2:21]1>>[CH2:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:12][C@@H:3]([CH2:1][N:20]2[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22][CH2:21]2)[NH:4]1

Participants

3

Reactant 2

HCID 79341Piperidin-4-olHCID 22861260(S)-tert-Butyl 3-formyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 86718897(S)-1-((1,2,3,4-Tetrahydroisoquinolin-3-yl)methyl)piperidin-4-ol

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 piperidin-4-ol (26 mg, 0.26 mmol) provided a crude oil which was used without purification in the preparation of Example 110. MS(ESI+) m/z 247.2 (M+H)+.

Workup

  1. customprovided a crude oil which
  2. customwas used without purification in the preparation of Example 110

Sources & evidence

ORD record
ord-92084ecb9ac340b1ab262a04d4ff7817
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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