Triethylamine → HCID 58551320, compound

HRID 1908159Notes

Reaction equation

HRID 1908159 reaction equation
[CH2:1]([C:3]1[CH:31]=[CH:30][C:6]([C:7]([N:9]2[CH2:29][CH2:28][C:12]3([C:17]4=[CH:18][CH:19]=[CH:20][N:16]4[C:15]4[CH:21]=[CH:22][C:23]([C:25](O)=[O:26])=[CH:24][C:14]=4[O:13]3)[CH2:11][CH2:10]2)=[O:8])=[CH:5][C:4]=1[O:32][CH3:33])[CH3:2].C(N(CC)CC)C.ClC(OCC(C)C)=O.[BH4-].[Na+]>O1CCCC1.O>[CH2:1]([C:3]1[CH:31]=[CH:30][C:6]([C:7]([N:9]2[CH2:10][CH2:11][C:12]3([O:13][C:14]4[CH:24]=[C:23]([CH2:25][OH:26])[CH:22]=[CH:21][C:15]=4[N:16]4[CH:20]=[CH:19][CH:18]=[C:17]34)[CH2:28][CH2:29]2)=[O:8])=[CH:5][C:4]=1[O:32][CH3:33])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 4311764Sodium borohydrideHCID 58551346HCID 58551346, compound

Product 1

HCID 58551320HCID 58551320, compoundYield 63.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 1-(4-ethyl-3-methoxy-benzoyl)spiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-7′-carboxylic acid (550 mg, 1.2 mmol) in tetrahydrofuran (2.2 mL) at 0° C. was added triethylamine (200 μL, 1.4 mmol) then isobutyl chloroformate (180 μL, 1.4 mmol). The mixture was stirred for 30 min then filtered. The filtrate was added dropwise to a solution of sodium borohydride (70 mg, 1.8 mmol) in water (770 μL) at 0° C. The mixture was allowed to slowly reach room temperature before it was concentrated to ⅓ volume, diluted with ethyl acetate and washed with 1M HCl. The organics were dried over sodium sulfate, filtered and evaporated to yield (4-ethyl-3-methoxyphenyl)(7-(hydroxymethyl)spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-yl)methanone (330 mg, 62%). ESI-MS m/z calc. 432.5. found 433.5 (M+1)+; Retention time: 1.78 minutes (3 min run).

Workup

  1. filtrationthen filtered
  2. customwas allowed to slowly reach room temperature before it
  3. concentrationwas concentrated
  4. additiondiluted with ethyl acetate
  5. washwashed with 1M HCl
  6. dry with materialThe organics were dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-d480c0a8756b4e0f8bcdbb3f2ebccf5f
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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