Lithium borohydride → [2-(2-Cyano-5-hydroxymethyl-phenoxy)-ethyl]-carbamic acid tert-butyl ester

HRID 1585910Notes

Reaction equation

HRID 1585910 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[C:6]([O:12][CH2:13][CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:5]=1.[Li+].[BH4-]>C1COCC1>[C:19]([O:18][C:16](=[O:17])[NH:15][CH2:14][CH2:13][O:12][C:6]1[CH:5]=[C:4]([CH2:3][OH:2])[CH:9]=[CH:8][C:7]=1[C:10]#[N:11])([CH3:22])([CH3:20])[CH3:21]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 540915033-(2-tert-Butoxycarbonylamino-ethoxy)-4-cyano-benzoic acid methyl ester

Product 1

HCID 53993861[2-(2-Cyano-5-hydroxymethyl-phenoxy)-ethyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

3-(2-tert-Butoxycarbonylamino-ethoxy)-4-cyano-benzoic acid methyl ester from Step 2 (346 mg, 1.08 mmol) was dissolved in THF (5.5 ml). LiBH4 in THF (2M, 1.1 ml, 2.16 mmol) was added. The reaction mixture was heated to 70° C. for 3 hours. The reaction was quenched carefully with 3N HCl and then extracted with EtOAc (3×10 mL). The organic layers were combined, washed with brine, dried (MgSO4), filtered and concentrated to yield the desired compound.

Workup

  1. customThe reaction was quenched carefully with 3N HCl
  2. extractionextracted with EtOAc (3×10 mL)
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1bdfb564d4c4439982b369e02d0f7359
Source dataset
uspto-grants-1999_08
Patent number
US05939439

Reaction notes

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