Diisopropylethylamine → 3-(4-Tert-butoxycarbonylaminophenyl)propanol

HRID 1375725Notes

Reaction equation

HRID 1375725 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17](O)=[O:18])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[BH4-].[Na+]>C1COCC1.C(OCC)(=O)C.CCCCCCC>[OH:18][CH2:17][CH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 4311764Sodium borohydrideHCID 170401113-(4-{[(Tert-butoxy)carbonyl]amino}phenyl)propanoic acid

Product 1

HCID 219940133-(4-Tert-butoxycarbonylaminophenyl)propanolYield 49%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21899848Ethylacetate heptaneSolvent

Procedure

3-{4-[(tert-Butoxycarbonyl)amino]phenyl}propanoic acid (1.33 g, 5.013 mmol) and BOP reagent (2.882 g, 6.517 mmol) were mixed in THF (30 ml). DIPEA (907 mg, 7.018 mmol) was added. The mixture was stirred for 10 minutes. Sodium borohydride (246 mg, 6.517 mmol) was added. The mixture was stirred for 30 minutes more and then evaporated to dryness. Ethyl acetate and water were added into the residue. The organic phase was washed with water and brine and dried with magnesium sulfate. The solvent was evaporated and an oil mixture was obtained. Column chromatography of the oil on silica gel using ethyl acetate/heptane (10:90, then 25:75) as eluant gave the desired oil product (616 mg), yield 49%.

Workup

  1. stirringThe mixture was stirred for 30 minutes more
  2. customevaporated to dryness
  3. additionEthyl acetate and water were added into the residue
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried with magnesium sulfate
  6. customThe solvent was evaporated
  7. customan oil mixture was obtained

Sources & evidence

ORD record
ord-976cd2dc782f42449d27f983e2fed0a0
Source dataset
uspto-grants-2007_01
Patent number
US07169810B2

Reaction notes

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