Tetrahydrofuran → HCID 67542919, compound

HRID 1809789Notes

Reaction equation

HRID 1809789 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:15]=[C:16]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:17]=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C[O:29]CC1>O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C@H:11]([C:14]2[CH:15]=[C:16]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:17]=[CH:18][CH:19]=2)[C@@H:12]([OH:29])[CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 19705303HCID 19705303, compound

Product 1

HCID 67542919HCID 67542919, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

To a stirred mixture of the title A compound, 4-biphenyl-3-yl-3,6,dihydro-2H-pyridine-1-carboxylic acid t-butyl ester (2.57 g, 7.66 mmol) and 6 mL of dry THF is added dropwise under argon at 5° C. a 1M borane-tetrahydrofuran complex solution (11 mL, 11 mmol) within 15 min. The reaction mixture is stirred for 10 min. at 5° C. and for 1 h at RT. NaBO3 (3.38 g, 22 mmol) is then added in several portions followed by H2O (10 mL). After 2 h at RT, the reaction mixture is extracted twice with ethyl acetate. The combined organic extracts are dried (Na2SO4) and evaporated in vacuo. Flash chromatography of the residue (SiO2, hexane/ethyl acetate) affords (3R*,4R*)-4-biphenyl-3-yl-3-hydroxy-piperidine-1-carboxylic acid t-butyl ester as a white amorphous solid: MS (after treatment with trifluoroacetic acid) 254.3 [M+H—C5H8O2]+; Rf 0.10 (hexane/ethyl acetate 8:2).

Workup

  1. waitAfter 2 h at RT
  2. extractionthe reaction mixture is extracted twice with ethyl acetate
  3. dry with materialThe combined organic extracts are dried (Na2SO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-e4345caf6b194b0ab9edf1cf4ed97e5c
Source dataset
uspto-grants-2013_01
Patent number
US08362040B2

Reaction notes

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