Methylamine → HCID 59201732, compound

HRID 451883Notes

Reaction equation

HRID 451883 reaction equation
CC1C=CC(S(O[CH2:12][C@@H:13]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:14][C@H:15]2[CH2:22][CH2:21][C:18]3([CH2:20][CH2:19]3)[O:17][CH2:16]2)(=O)=O)=CC=1.[NH2:31][CH3:32]>C(O)C>[CH2:20]1[C:18]2([CH2:21][CH2:22][C@H:15]([CH2:14][C@H:13]([NH:23][C:24](=[O:25])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:12][NH:31][CH3:32])[CH2:16][O:17]2)[CH2:19]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 59201644HCID 59201644, compound

Product 1

HCID 59201732HCID 59201732, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

The (S)-2-(tert-butoxycarbonylamino)-3-((R)-4-oxaspiro[2.5]oct-6-yl)propyl 4-methylbenzenesulfonate was dissolved in 100 mL of 33% NH2Me in ethanol. The mixture was heated to 50° C. for 3 hr. After this time LC/MS analysis shows formation of the desired amine. The solution was evaporated and the residue taken up in EtOAc, washed with 10% K2CO3, brine, dried over Na2SO4, filtered and evaporated. The tert-butyl (S)-1-((R)-4-oxaspiro[2.5]oct-6-yl)-3-(methylamino)propan-2-ylcarbamate was used directly in the next step with no further purification. MS ESI +ve m/z 301 (M+1).

Workup

  1. customThe solution was evaporated
  2. washwashed with 10% K2CO3, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe tert-butyl (S)-1-((R)-4-oxaspiro[2.5]oct-6-yl)-3-(methylamino)propan-2-ylcarbamate was used directly in the next step with no further purification

Sources & evidence

ORD record
ord-e57f86a4b7a94e2894ccac5e0a005962
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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