Aluminium lithium hydride → tert-Butyl (3-(3,5-bis(hydroxymethyl)phenoxy)propyl)(isobutyl)carbamate

HRID 59001Notes

Reaction equation

HRID 59001 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]([C:23](OC)=[O:24])[CH:16]=[C:17]([CH:22]=1)[C:18](OC)=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:24][CH2:23][C:15]1[CH:14]=[C:13]([CH:22]=[C:17]([CH2:18][OH:19])[CH:16]=1)[O:12][CH2:11][CH2:10][CH2:9][N:8]([CH2:27][CH:28]([CH3:29])[CH3:30])[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 117704517Dimethyl 5-(3-((tert-butoxycarbonyl)(isobutyl)amino)propoxy)isophthalate

Product 1

HCID 131737053tert-Butyl (3-(3,5-bis(hydroxymethyl)phenoxy)propyl)(isobutyl)carbamateYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethyl 5-(3-((tert-butoxycarbonyl)(isobutyl)amino)propoxy)isophthalate (0.60 g, 1.44 mmol) in THF (10 mL) was added LiAlH4 (0.30 g, 7.89 mmol). The reaction mixture was stirred for 8 h and subsequently quenched with 2N HCl (10 mL) and extracted with Et2O (2×25 mL) and EtOAc (2×25 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure to afford the desired product (0.28 g, 54%) as an oil, which was used without further purification.

Workup

  1. customsubsequently quenched with 2N HCl (10 mL)
  2. extractionextracted with Et2O (2×25 mL) and EtOAc (2×25 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-acef6d5fc1db4ae487e9af567e2a0435
Source dataset
uspto-grants-2016_09
Patent number
US09439433B2

Reaction notes

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