Hexane → Tert-butyl 6-[(cyclopropylmethoxy)methyl]-6-hydroxy-1,4-oxazepane-4-carboxylate

HRID 401814Notes

Reaction equation

HRID 401814 reaction equation
ClC1C=C(C(OO)=[O:9])C=CC=1.[OH:12][CH2:13][CH:14]1[CH2:20][O:19][CH2:18][CH2:17][N:16]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:15]1.CC[CH2:30][CH2:31][CH2:32][CH3:33]>C(Cl)Cl>[CH:32]1([CH2:33][O:12][CH2:13][C:14]2([OH:9])[CH2:20][O:19][CH2:18][CH2:17][N:16]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:15]2)[CH2:30][CH2:31]1

Participants

5

Reactant 3

HCID 8058HexaneHCID 70297m-Chloroperbenzoic acidHCID 57732267Tert-butyl 6-(hydroxymethyl)-1,4-oxazepane-4-carboxylate

Product 1

HCID 68531565Tert-butyl 6-[(cyclopropylmethoxy)methyl]-6-hydroxy-1,4-oxazepane-4-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

70-75% m-Chlorobenzenecarboperoxoic acid (145 g, 0.59 mol, 1.2 eq) was added in portions to a stirred solution of tert-butyl 6-(hydroxymethyl)-1,4-oxazepane-4-carboxylate (Preparation 79, 107 g, 0.5 mol, 1 eq) in DCM (1.0 L) that caused heating of the mixture. The reaction mixture was stirred for 24 h at room temperature, then diluted with hexane (500 mL) and filtered. The separated precipitate was washed on a filter with DCM/hexane mixture, and the combined filtrate was washed with aqueous potassium carbonate, dried over sodium sulfate, and evaporated. The residue was vacuum-dried to give title compound (117 g, 0.51 mol, 96%).

Workup

  1. temperaturecaused heating of the mixture
  2. filtrationfiltered
  3. washThe separated precipitate was washed on
  4. filtrationa filter with DCM/hexane mixture
  5. washthe combined filtrate was washed with aqueous potassium carbonate
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe residue was vacuum-dried

Sources & evidence

ORD record
ord-ed933b6df9e04b2c89e88667bd527058
Source dataset
uspto-grants-2014_06
Patent number
US08741934B2

Reaction notes

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