Methanol → Tert-butyl ((6-(hydroxymethyl)-1,2,3,4-tetrahydronaphthalen-2-YL)methyl)carbamate

HRID 1061018Notes

Reaction equation

HRID 1061018 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:20](OC)=[O:21])[CH:16]=2)[CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.CCCCCC.CO>ClCCl>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:20][OH:21])[CH:16]=2)[CH2:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 8058HexaneHCID 21225700DiisobutylaluminumhydrideHCID 22709912Methyl 6-(((tert-butoxycarbonyl)amino)methyl)-5,6,7,8-tetrahydronaphthalene-2-carboxylate

Product 1

HCID 22709613Tert-butyl ((6-(hydroxymethyl)-1,2,3,4-tetrahydronaphthalen-2-YL)methyl)carbamateYield 72.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In dichloromethane (10 ml), (2RS)-2-(N-tert-butoxycarbonylaminomethyl)-6-methoxycarbonyl-1,2,3,4-tetrahydronaphthalene (0.47 g) was dissolved, followed by the dropwise addition of diisobutylaluminum hydride (a 0.95M hexane solution, 3.6 ml) at an external temperature of −78° C. The resulting mixture was stirred for 90 minutes without changing the temperature. Methanol was added to the reaction mixture, followed by heating to room temperature. The insoluble matter was filtered off through Celite. The filtrate was concentrated under reduced pressure. The concentrate was diluted with dichloromethane, washed with water and dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by chromatography on a silica gel column (hexane:ethyl acetate=3:1), whereby colorless crystals (0.31 g, 72%) were obtained. A portion of the crystals was recrystallized from a mixed solvent of hexane and ethyl acetate, whereby colorless crystals were obtained.

Workup

  1. filtrationThe insoluble matter was filtered off through Celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. additionThe concentrate was diluted with dichloromethane
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe residue obtained
  7. distillationby distilling off the solvent under reduced pressure
  8. customwas purified by chromatography on a silica gel column (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-9b2711d0c0d84016bcd2fc80b4778518
Source dataset
uspto-grants-2003_02
Patent number
US06525042B1

Reaction notes

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