Benzyl Alcohol → phenylmethyl (2-methyl-2,3-dihydro-1H-inden-2-yl)carbamate

HRID 70280Notes

Reaction equation

HRID 70280 reaction equation
C[C:2]1([C:11](O)=O)[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1.C([N:16]([CH2:19]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:28])C=CC=CC=1.[CH2:38]([OH:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C1C=CC=CC=1.Cl>[CH3:11][C:2]1([NH:16][C:19](=[O:28])[O:45][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:10]1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 153388422-methyl-2,3-dihydro-1H-indene-2-carboxylic acid

Product 1

HCID 57585915phenylmethyl (2-methyl-2,3-dihydro-1H-inden-2-yl)carbamate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 313Hydrochloric AcidSolvent

Procedure

To a solution of 2-methyl-2,3-dihydro-1H-indene-2-carboxylic acid (0.200 g, 1.14 mmol) and triethylamine (0.17 mL, 1.2 mmol) in benzene (2 mL) at 0° C. was added diphenyl phosphorylazide (0.257 g, 1.19 mmol). The mixture was stirred 15 min, benzyl alcohol (0.123 mL, 1.19 mmol) was added and the reaction was heated under reflux for 16 hours. Upon cooling, the mixture was diluted with 10% HCl and extracted with ethyl acetate (2×25 mL). Combined organics were washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes) affording the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 1.55 (s, 3H), 2.98 (d, J=15.9 Hz, 2 H), 3.28 (d, J=15.9 Hz, 2 H), 7.12-7.18 (m, 4H), 7.29-7.37 (m, 5H).

Workup

  1. temperaturethe reaction was heated
  2. temperatureunder reflux for 16 hours
  3. temperatureUpon cooling
  4. extractionextracted with ethyl acetate (2×25 mL)
  5. washCombined organics were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-91c6aeb92dcd44c79a8a6341eb4ee6ec
Source dataset
uspto-grants-2014_09
Patent number
US08822518B2

Reaction notes

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