Triethylamine → tert-Butyl 1-benzyl-7-((cyclopropylmethylsulfonamido)methyl)-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate

HRID 82867Notes

Reaction equation

HRID 82867 reaction equation
[NH2:1][CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH:10]2[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH:35]1([CH2:38][S:39](Cl)(=[O:41])=[O:40])[CH2:37][CH2:36]1>ClCCl>[CH2:13]([CH:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([CH2:2][NH:1][S:39]([CH2:38][CH:35]3[CH2:37][CH2:36]3)(=[O:41])=[O:40])[CH:12]=2)[CH2:7][CH2:8][CH:9]1[NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:26])[CH3:25])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 14106996Cyclopropylmethanesulphonyl chlorideHCID 57471193Tert-butyl [7-(aminomethyl)-1-benzyl-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate

Product 1

HCID 86685686tert-Butyl 1-benzyl-7-((cyclopropylmethylsulfonamido)methyl)-1,2,3,4-tetrahydronaphthalen-2-ylcarbamateYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl 7-(aminomethyl)-1-benzyl-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate (0.600 g, 1.637 mmol) was suspended in dichloromethane (5 mL) and triethylamine (0.228 mL, 1.637 mmol) and cooled to 0° C. Cyclopropylmethanesulfonyl chloride (0.253 g, 1.637 mmol) was added. The solid immediately dissolved. The mixture was stirred overnight and then diluted with dichloromethane and washed with brine (3×50 mL). The organic extract was collected dried on MgSO4 and evaporated under reduced pressure. The residue was purified by flash-chromatography on silica gel (100% dichloromethane 5 minutes then gradient to 1% MeOH in dichloromethane). Product was isolated as white powder (601.9 mg, 1.24 mmol, 76%).

Workup

  1. dissolutionThe solid immediately dissolved
  2. washwashed with brine (3×50 mL)
  3. extractionThe organic extract
  4. customwas collected
  5. customdried on MgSO4
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash-chromatography on silica gel (100% dichloromethane 5 minutes

Sources & evidence

ORD record
ord-6a78cc3950524ac5afcb5fdfa61290cc
Source dataset
uspto-grants-2014_09
Patent number
US08846741B2

Reaction notes

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