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Acetic Acid → 4-[3-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-propyl]-[1,4]diazepan-5-one

HRID 1096242
Notes
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Reaction equation

HRID 1096242 reaction equation
Cl.[CH2:2]1[C:4]2([CH2:9][CH2:8][NH:7][CH2:6][C@H:5]2[OH:10])[CH2:3]1.CCN(CC)CC.CC(O)=O.C(OC([N:29]1[CH2:35][CH2:34][C:33](=[O:36])[N:32]([CH2:37][CH2:38][CH:39]=O)[CH2:31][CH2:30]1)=O)(C)(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:10][C@@H:5]1[CH2:6][N:7]([CH2:39][CH2:38][CH2:37][N:32]2[C:33](=[O:36])[CH2:34][CH2:35][NH:29][CH2:30][CH2:31]2)[CH2:8][CH2:9][C:4]21[CH2:3][CH2:2]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 44541812(4S)-6-Azaspiro[2.5]octan-4-ol hydrochloride2×HCID 866158685-Oxo-4-(3-oxo-propyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Product

1
HCID 667832354-[3-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-propyl]-[1,4]diazepan-5-oneYield 71.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of (S)-6-aza-spiro[2.5]octan-4-ol hydrochloride (intermediate 2) 0.16 g (1 mmol) in CH2Cl2 (5 ml) was added Et3N 0.14 ml (1 mmol) and AcOH 0.11 ml (2 mmol) followed by a solution of 5-oxo-4-(3-oxo-propyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester 0.34 g (1 mmol) in CH2Cl2 (5 ml) and finally sodium triacetoxyborohydride 0.25 g (1 mmol). The mixture was stirred for 1 h after which time sat. aq. NaHCO3. solution was added, the reaction extracted with in CH2Cl2, dried (Na2SO4) and concentrated. The residue was taken up in 1 M HCl solution in dioxane (10 ml), stirred for 10 minutes before the solvent was evaporated. The residue was then dissolved in sat. aq. NaHCO3. solution the water removed by evaporation, and the solid extracted with CH2Cl2:MeOH (9:1). Concentration afforded the title compound 0.2 g (71%) as yellow oil. MS: 282.1 (MH+).

Workup

  1. additionsolution was added
  2. extractionthe reaction extracted with in CH2Cl2
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customwas evaporated
  6. dissolutionThe residue was then dissolved in sat. aq. NaHCO3
  7. customsolution the water removed by evaporation
  8. extractionthe solid extracted with CH2Cl2:MeOH (9:1)
  9. concentrationConcentration

Sources & evidence

ORD record
ord-602058d10fad49f8a2294a952cf19aea
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08138175B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes