Water → HCID 68312852, compound

HRID 1530717Notes

Reaction equation

HRID 1530717 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C@@H:13]([CH:17]([NH:24][CH2:25][CH:26]=[CH2:27])[CH2:18][C:19](OCC)=[O:20])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Li+].O>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C@@H:13]([CH:17]([NH:24][CH2:25][CH:26]=[CH2:27])[CH2:18][CH2:19][OH:20])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 68313077HCID 68313077, compound

Product 1

HCID 68312852HCID 68312852, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (R)-3-(1-allylamino-2-ethoxycarbonylethyl)piperidine-1-carboxylic acid benzyl ester (0.427 g, 1.14 mmol) in THF (20 mL) was added a solution of lithium borohydride in THF (2M, 5.7 mL, 11.4 mmol). The mixture was stirred at RT for 10 min then at 40° C. for 22 h. After cooling to RT, water was added with initial caution. The mixture was extracted twice with EtOAc, and the combined organic phases were washed with water, followed by brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 2-8% 2M NH3/MeOH in DCM) affording the title compound (0.264 g, 70%) as a colourless gum. LCMS (Method B): RT 2.00 min [M+H]+ 333.

Workup

  1. waitat 40° C. for 22 h
  2. temperatureAfter cooling to RT
  3. extractionThe mixture was extracted twice with EtOAc
  4. washthe combined organic phases were washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by column chromatography (Si-PCC, gradient 2-8% 2M NH3/MeOH in DCM)

Sources & evidence

ORD record
ord-7a79db9b72554b199ada8d6eab57a103
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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