Triethylamine → HCID 57947757, compound

HRID 340903Notes

Reaction equation

HRID 340903 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.ClC(OCC(C)C)=O.[BH4-].[Na+]>C1COCC1.O>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:10][OH:11])[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 4311764Sodium borohydrideHCID 11288857350832-82-5

Product 1

HCID 57947757HCID 57947757, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-2-(tert-butoxycarbonylamino)-6-methoxy-6-oxohexanoic acid (23.5 g, 85 mmol) in anhydrous THF (100 mL) was added Et3N (14.2 mL, 102 mmol, 1.2 equiv.). The solution was cooled down to 0° C. and isobutyl chloroformate (12.2 mL, 93.5 mmol, 1.1 equiv.) was added dropwise. The solution was stirred for 30 min. The precipitate was filtered off. The filtrate was cooled down to 0° C. and a suspension of sodium borohydride (6.5 g, 170 mmol, 2 equiv.) in H2O (3 mL) was added in one portion. The reaction was stirred for 1 h, and quenched with saturated NH4Cl. THF was removed. The residue was dissolved into EtOAc (400 mL) and extracted with saturated NH4Cl twice. The organic layers were combined, dried and concentrated. The residue was purified on silica gel column (hexanes/EtOAc 1:1) to give (S)-methyl 5-(tert-butoxycarbonylamino)-6-hydroxyhexanoate (20 g, 90%) as a colorless oil. LRMS (M-Boc+H+) m/z 162.1.

Workup

  1. filtrationThe precipitate was filtered off
  2. temperatureThe filtrate was cooled down to 0° C.
  3. additionwas added in one portion
  4. stirringThe reaction was stirred for 1 h
  5. customquenched with saturated NH4Cl
  6. customTHF was removed
  7. dissolutionThe residue was dissolved into EtOAc (400 mL)
  8. extractionextracted with saturated NH4Cl twice
  9. customdried
  10. concentrationconcentrated
  11. customThe residue was purified on silica gel column (hexanes/EtOAc 1:1)

Sources & evidence

ORD record
ord-27bdccb029de47d896122b4119d10f4d
Source dataset
uspto-grants-2014_11
Patent number
US08895582B2

Reaction notes

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