Water → HCID 86669702, compound

HRID 1623969Notes

Reaction equation

HRID 1623969 reaction equation
[BH4-].[Na+].O.C([O:6][C:7]([C:9]1([NH:13][C:14]([C:16]2[C:17]3[CH2:18][C@H:19]4[CH2:30][C@H:20]4[C:21]=3[N:22]([C:24]3[CH:29]=[N:28][CH:27]=[CH:26][N:25]=3)[N:23]=2)=[O:15])[CH2:12][CH2:11][CH2:10]1)=O)C>O1CCOCC1>[OH:6][CH2:7][C:9]1([NH:13][C:14]([C:16]2[C:17]3[CH2:18][C@H:19]4[CH2:30][C@H:20]4[C:21]=3[N:22]([C:24]3[CH:29]=[N:28][CH:27]=[CH:26][N:25]=3)[N:23]=2)=[O:15])[CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 68182517HCID 68182517, compound

Product 1

HCID 86669702HCID 86669702, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of sodium borohydride (0.206 g, 5.44 mmol) in dioxane (2.0 mL) with water (1.0 mL) was added 1-[((1aR,5aR)-2-pyrazin-2-yl-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carbonyl)-amino]-cyclobutanecarboxylic acid ethyl ester (1.0 g, 2.72 mmol) at 0° C. The mixture was stirred at room temperature until the starting materials were consumed. The mixture was concentrated and added 2 M HCl was added to adjust pH to 3. The isolated precipitate was dissolved in DCM and purified by silica gel column chromatography to give the title compound (0.5 g) as a solid. LCMS m/z=326.3 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 0.47 (dd, J=8.0 and 4.7 Hz, 1H), 1.26 (td, J=7.8 and 4.9 Hz, 1H), 1.85-2.26 (m, 2H), 2.21-2.40 (m, 5H), 2.73-2.78 (m, 1H), 2.91 (d, J=16.8 Hz, 1H), 3.00 (dd, J=16.6 and 6.3 Hz, 1H), 3.90 (s, 2H), 7.21 (bs, NH, 1H), 8.42 (dd, J=2.3 and 1.5 Hz, 1H), 8.51 (d, J=2.5 Hz, 1H), 9.26 (d, J=1.4 Hz, 1H).

Workup

  1. customwere consumed
  2. concentrationThe mixture was concentrated
  3. additionadded 2 M HCl
  4. additionwas added
  5. dissolutionThe isolated precipitate was dissolved in DCM
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-07375aa3336c43dab87f188f19b19c4c
Source dataset
uspto-grants-2014_07
Patent number
US08778950B2

Reaction notes

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