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

HRID 1421732Notes

Reaction equation

HRID 1421732 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 (2 M, 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. 1H NMR (400 MHz, CDCl3) δ 7.48 (d, 1H, d, J=4.54 Hz), 7.10 (s, 1H), 6.98 (d, 1H, J=4.30 Hz), 5.10 (bs, 1H, NH), 4.76 (s, 2H), 4.12 (m, 2H), 3.55 (m, 2H), 1.40 (s, 9H).

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-a0acbed2a0eb4565a5b550c0c4d452be
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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