Water → tert-Butyl [4-(hydroxymethyl)benzyl]carbamate

HRID 2277004Notes

Reaction equation

HRID 2277004 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O>C1COCC1.O1CCOCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:14][OH:15])=[CH:17][CH:18]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 962WaterHCID 8536054-(((tert-Butoxycarbonyl)amino)methyl)benzoic acid

Product 1

HCID 2794813tert-Butyl [4-(hydroxymethyl)benzyl]carbamateYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
0 °C

Procedure

LiAl4 (227 mg, 5.97 mmol) was slurried in a mixture of THF (5 mL) and dioxane (5 mL) and cooled to 0° C. under an atmosphere of N2. 4-(tert-Butoxycarbonylamino-methyl)-benzoic acid was dissolved in a mixture of THF (5 mL) and dioxane (5 mL) and added to the chilled solution drop-wise over 15 min. The reaction mixture was allowed to warm to r.t and stirred for 16 h. Water (1 mL) was added to the reaction mixture which was then filtered through celite. The filtrate was evaporated to dryness and the residue partitioned between EtOAc (25 mL) and water (25 mL). The aqueous layer was extracted with EtOAC (2×25 mL), the organic layers combined, dried (Na2SO4) and evaporated to dryness to afford the desired product (460 mg, 100%). m/z 260 [M++Na]+

Workup

  1. additionadded to the chilled solution drop-wise over 15 min
  2. temperatureto warm
  3. filtrationwas then filtered through celite
  4. customThe filtrate was evaporated to dryness
  5. customthe residue partitioned between EtOAc (25 mL) and water (25 mL)
  6. extractionThe aqueous layer was extracted with EtOAC (2×25 mL)
  7. dry with materialdried (Na2SO4)
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-f03363f11d3e4b14ab178055353040f1
Source dataset
uspto-grants-2015_09
Patent number
US09133104B2

Reaction notes

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