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

HRID 547667Notes

Reaction equation

HRID 547667 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.Cl>C1C=CC=CC=1>[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 5

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 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)carbamateYield 84.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution 2-methyl-2,3-dihydro-1H-indene-2-carboxylic acid (0.200 g, 1.14 mmol) and triethylamine (0.166 mL, 1.19 mmol) in 2 mL of benzene at to 0 degrees Centigrade was added diphenyl phosphorylazide (0.257 g, 1.19 mmol). The reaction mixture was stirred for 15 minutes and benzyl alcohol (0.123 mL, 1.19 mmol) was added and the reaction was heated to reflux for 16 hours, then cooled and 10% HCl was added. The organics were extracted 2×25 mL ethyl acetate, then washed 1× brine, dried (Na2SO4), filtered and concentrated. The residue was chromatographed on silica using 5:1 hexanes/ethyl acetate to give 0.271 g of the phenylmethyl (2-methyl-2,3-dihydro-1H-inden-2-yl)carbamate.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 16 hours
  3. temperaturecooled
  4. extractionThe organics were extracted 2×25 mL ethyl acetate
  5. washwashed 1× brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was chromatographed on silica using 5:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-8c8181c7c4ff4b5db6d0d37b1bd0c091
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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